ORGANIC ELECTROLUMINESCENT DEVICE

• US 20090179554A1
• Filed: 05/02/2007
• Published: 07/16/2009
• Est. Priority Date: 05/11/2006
• Status: Active Grant

• Current Assignee: Idemitsu Kosan Company Limited
• Original Assignee: Idemitsu Kosan Company Limited
• Inventors: Kuma, Hitoshi, Hosokawa, Chishio, Yamamoto, Hiroshi
• Granted Patent: US 8,076,839 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/19 Tandem OLEDs
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

An organic electroluminescence device (1) including: an anode (20) and a cathode (50), at least two organic emitting layers (30), (32) and (34) interposed between the anode and the cathode, and at least one intermediate connection layer (40) and (42) being provided between the organic emitting layers (30), (32) and (34), the intermediate connection layer (40) and (42) comprising an acceptor layer, a donor layer and an electron-transporting material layer being stacked in this order from the cathode (50), the electron-transporting material layer containing a non-complex compound with a nitrogen-containing heterocyclic structure.

Claims

1. An organic electroluminescence device comprising:

an anode and a cathode,

at least two organic emitting layers interposed between the anode and the cathode, and

at least one intermediate connection layer being provided between the organic emitting layers,

the intermediate connection layer comprising an acceptor layer, a donor layer and an electron-transporting material layer being stacked in this order from the cathode,

the electron-transporting material layer containing a non-complex compound with a nitrogen-containing heterocyclic structure.

2. The organic electroluminescence device according to claim 1, wherein the nitrogen-containing heterocyclic structure is a nitrogen-containing five-membered heterocyclic structure.

3. The organic electroluminescence device according to claim 1, wherein the non-complex compound with a nitrogen-containing heterocyclic structure in the electron-transporting material layer is a compound represented by the following formula (1):

wherein R¹ to R⁸ are independently a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group substituted by a substituted or unsubstituted aryl group having 5 to 50 ring atoms, a halogen atom, a cyano group, a nitro group, a hydroxy group or a carboxy group; and

a pair of adjacent substituents of R¹ to R⁸ may be bonded to each other to form an aromatic ring or a heterocyclic ring.

4. The organic electroluminescence device according to claim 1, wherein the non-complex compound with a nitrogen-containing heterocyclic structure in the electron-transporting material layer is a compound represented by the following formula (2):

wherein R⁹ to R²⁰ are independently a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaryl group having 5 to 60 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group substituted by a substituted or unsubstituted aryl group having 5 to 50 ring atoms, a halogen atom, a cyano group, a nitro group, a hydroxy group or a carboxy group;

adjacent groups of R⁹ to R²⁰ may be bonded to each other to form an aromatic ring, and at least one of R⁹ to R²⁰ is a substituent represented by the following formula;

wherein L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms or a substituted or unsubstituted fluorenylene group;

Ar¹ is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridinylene group or a substituted or unsubstituted quinolinylene group;

Ar² is a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 ring atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 ring atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 ring atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, an amino group substituted by a substituted or unsubstitued aryl group having 5 to 50 ring atoms, a halogen atom, a cyano group, a nitro group, a hydroxy group or a carboxy group.

5. The organic electroluminescence device according to claim 4, wherein the non-complex compound with a nitrogen-containing heterocyclic structure in the electron-transporting material layer is a compound represented by the following formula:

wherein R^1a to R^6c, L_a to L_c and Ar^1a to Ar^2c are the same as R⁹ to R²⁰, L, Ar¹ and Ar² in the above formula (2), respectively.

6. The organic electroluminescence device according to claim 1, wherein the donor of the donor layer is an alkaline metal, an alkaline earth metal, a rare earth metal, or an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal and an organic complex of a rare earth metal.

7. The organic electroluminescence device according to claim 1, wherein the acceptor of the acceptor layer is an organic compound having an electron-attracting substituent or an electron-deficient ring.

8. The organic electroluminescence device according to claim 7, wherein the acceptor in the acceptor layer is a quinoide derivative, an arylborane derivative, a thiopyrane dioxide derivative, a naphthalimide derivative or a hexaazatriphenylene derivative.